Guilford Family-Friendly Fall Activities 2026

43 family-friendly fall activities in Guilford and nearby

Illustration of clay figures in costumes mingling among striped market tents and pumpkin displays under orange autumn trees (Spooktacular on the Green)

Spooktacular on the Green

Sun, Oct 25

Guilford Free

Scary stories, live performers, music, and trunk-or-treat on the green.

Bishop's Fall Festival

Sep 5 – Nov 1

Guilford $

Features a four-acre corn maze, wagon rides, and pick-your-own fruit.

Illustration of a ghost and a small witch carrying a pumpkin bucket on a sidewalk past glowing porches on an autumn street (The Mayer Center Fear-Not Halloween Fun Day)

The Mayer Center Fear-Not Halloween Fun Day

Sat, Oct 17

Essex 14 mi Free

A sensory-friendly and not-so-scary Halloween event with trunk-or-treat.

Illustration of two tiny costumed figures near a flag among tall golden cornstalks, with small farm houses and pumpkins (Lyman Orchards Pick Your Own Pumpkins)

Lyman Orchards Pick Your Own Pumpkins

Middlefield 14 mi

Pick sugar and carving pumpkins overlooking the Connecticut River Valley.

Illustration of a miniature carnival at dusk with a glowing ferris wheel, a small carousel, game booths and jack-o'-lanterns (Mountain Mist Halloween Harvest)

Mountain Mist Halloween Harvest

Sun, Oct 25

Meriden 15 mi $

Family Halloween fun featuring trunk or treat, llama petting, and carnival games.

Illustration of a ghost and two costumed kids trick or treating past glowing houses with pumpkins and autumn leaves at dusk (15th Annual Milford 5K Trick or Trot Run/Walk)

15th Annual Milford 5K Trick or Trot Run/Walk

Sat, Oct 31

Milford 20 mi $$$

Charity 5K run and walk featuring costume contests for Beth-El Center.

Seymour Pumpkin Festival

Sun, Sep 20

Seymour 21 mi Free

60th annual community festival with over 150 craft vendors

Boo Fest by the Beach

Sat, Oct 17

Milford 21 mi

Shoreline Halloween celebration with trick-or-treating, carriage rides, and family entertainment.

Illustration of a small clay figure on a path between tall golden cornstalks, with a red flag, pumpkins and a tiny cottage (Jones Family Farms Pumpkin Season)

Jones Family Farms Pumpkin Season

Sep 28 – Oct 31

Shelton 25 mi

Explore the farmyard, mini corn maze, walking trail, and farm animals.

Illustration of a giant grinning jack-o'-lantern float and costumed marchers parading along a tree-lined park path at dusk (Walnut Beach Halloween Pet Parade & Contest)

Walnut Beach Halloween Pet Parade & Contest

Sun, Oct 18

Milford 21 mi

Costumed pets walk the runway for an annual judged costume contest.

Illustration of a Halloween parade on a town street at dusk with a giant smiling pumpkin float and costumed children (Walnut Beach Halloween Parade)

Walnut Beach Halloween Parade

Sat, Oct 31

Milford 21 mi

Features a kids' costume parade and free ice cream in costume.

Lyman Orchards 2025 Corn Maze

Sep 5 – Nov 1

Middlefield 14 mi $

Four-acre maze with trivia celebrating 250 years of American history.

Prospect Pumpkin Festival

Sat, Oct 17

Hartford 21 mi

Community festival featuring a decorated car and truck costume parade.

Illustration of a pumpkin patch with many orange pumpkins, a scarecrow, a red wheelbarrow, hay and a wooden farm stand (Shore Line Trolley Museum Pumpkin Patch)

Shore Line Trolley Museum Pumpkin Patch

Oct 3 – Oct 25

East Haven 9 mi $$

Ride a historic trolley to pick your own sugar pumpkin.

Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees (The Great Pumpkin Festival)

The Great Pumpkin Festival

Sat, Oct 17

Stratford 22 mi

Features a pumpkin carving contest, costume parade, hayrides, and Public Safety Day.

Illustration of costumed children carrying pumpkin buckets along a winding path past glowing cottages at dusk (Shubert Theatre Free Family Fun Day)

Shubert Theatre Free Family Fun Day

Sun, Oct 25

New Haven 13 mi Free

Backstage trick-or-treat walking tour through the Shubert Theatre.

Illustration of clay figures walking past striped market stalls and pumpkins on a paved square with orange autumn trees (Corn Maze & Cider Donut Harvest Music Festival)

Corn Maze & Cider Donut Harvest Music Festival

Middlefield 15 mi $$

Pizza-themed corn maze with local CT pizza facts

Illustration of a child in a witch costume holding a pumpkin bucket on a leafy sidewalk lined with glowing houses at dusk (Bats, Barnacles & Broomsticks Halloween Party)

Bats, Barnacles & Broomsticks Halloween Party

Sat, Oct 24

Riverhead 26 mi

Aquarium Halloween celebration featuring trick-or-treating, crafts, and animal treats.

Foster Family Farm Fall Fun

Sep 12 – Nov 1

South Windsor 38 mi $$

Explore three corn mazes featuring twelve national park checkpoints and prizes.

Scarecrows Along Main

Oct 1 – Oct 31

Old Wethersfield 29 mi

Over 100 handmade scarecrows displayed along Main Street.

Illustration of a town square fall festival with striped pumpkin booths, costumed figures, and orange autumn trees (Center Moriches Fall Festival)

Center Moriches Fall Festival

Sun, Oct 18

Center Moriches 34 mi

Over 100 vendors, food trucks, and live music on Main Street.

Illustration of costumed children and two witches on a lawn with pumpkins, a small tent and orange autumn trees (Enchanted Forest Trail at Quogue Wildlife Refuge)

Enchanted Forest Trail at Quogue Wildlife Refuge

Oct 24 – Oct 25

Quogue 32 mi $

Costumed guided nature walk meeting whimsical characters for young children.

Illustration of two small ghosts and a witch with a black cat carrying pumpkin buckets on a street of cozy houses at dusk (West Hartford Halloween Stroll)

West Hartford Halloween Stroll

Sat, Oct 24

West Hartford 33 mi

Trick-or-treating, music, and giveaways for costumed children across town center.

Illustration of clay skeleton figures in folk outfits by an altar with lit candles, orange marigolds and paper banners (Día de Muertos Community Celebration)

Día de Muertos Community Celebration

Sat, Oct 24

Hartford 34 mi Free

Day of the Dead celebration with mariachi, Mexican folk dance, and ofrendas.

Illustration of a ghost, a witch and a pumpkin figure on a dusk street with glowing houses, autumn leaves and pumpkins (Gateway's Not-So-Scary Halloween Adventure)

Gateway's Not-So-Scary Halloween Adventure

Oct 10 – Oct 25

Bellport 39 mi $$

A family-friendly walk-through featuring goofy creatures and a treat at the end.

Illustration of a row of cars with open trunks decorated for Halloween at sunset with balloons, pumpkins and costumed kids (Hartford Turnpike Trunk or Treat 2026)

Hartford Turnpike Trunk or Treat 2026

Thu, Oct 22

Waterford 28 mi Free

Features food trucks, music, games, balloon twisting, and candy.

Castle Hill Farm Corn Maze

Sat, Oct 3

Newtown 34 mi $

Seven-acre corn maze featuring 30 game signs and an observation deck.

Happy HalloWINE Run & Walk

Sun, Nov 1

Stratford 25 mi $$

Scenic coastal 5K run and walk featuring wine, beer, and snacks.

Pumpkin Passage

Oct 3 – Nov 1

Oakdale 26 mi $$

Kid-friendly Halloween trail with glowing dinosaurs, animatronics, and live entertainment.

Halloween at the Farm

Sat, Oct 24

Yaphank 34 mi $

Trick-or-treat stations, unlimited wagon rides, farm animals, and a corn maze.

Illustration of a Halloween craft scene with clay kids, a friendly ghost, bats and glowing pumpkins under party bunting (Klingberg Family Centers Trunk or Treat)

Klingberg Family Centers Trunk or Treat

Thu, Oct 22

New Britain 26 mi

Free reflective tote bag for the first 250 children.

Manchester Fall Festival

Sat, Oct 10

Manchester 35 mi Free

Features live music, local crafts, and food treats for all ages.

Illustration of an older person handing out candy to costumed children on a glowing neighborhood porch at dusk (Chuck E. Cheese Boo-tacular Halloween Event)

Chuck E. Cheese Boo-tacular Halloween Event

Orange 16 mi $$

Nightly trick-or-treating and 500 bonus E-Tickets for costumed kids.

Illustration of costumed figures near striped booths and pumpkin displays on a grassy town square with orange autumn trees (Hall-O-Weekend Fall Festival)

Hall-O-Weekend Fall Festival

Milford 20 mi Free

Free, not-so-scary Halloween weekend for families in downtown Milford.

Illustration of two tiny costumed figures near a flag among tall golden cornstalks, with small farm houses and pumpkins (Wells Hollow Creamery Flashlight Maze)

Wells Hollow Creamery Flashlight Maze

Shelton 23 mi $$

"It's a Bug's Life" themed corn maze

Illustration of two tiny figures on a gravel path among golden cornstalks and pumpkins, with a red flag at sunset (Fair Weather Growers Fall Festival & Corn Maze)

Fair Weather Growers Fall Festival & Corn Maze

Cromwell 24 mi $$

16-acre farm transformed for fall fun

Illustration of a pumpkin patch with many orange pumpkins, curling vines, a wheelbarrow and a small farm stand at dusk (St. Peter's Community Pumpkin Patch)

St. Peter's Community Pumpkin Patch

Cheshire 19 mi $

Cheshire's beloved "Pumpkin Church" community tradition

Boomer's Boo Bash

Hamden 14 mi Free

Annual community Halloween celebration at Quinnipiac University

Illustration of two costumed trick or treaters with candy buckets on a dusk street of glowing houses and carved pumpkins (Safe Trick or Treat at The Shoppes)

Safe Trick or Treat at The Shoppes

WADING RIVER 25 mi Free

Safe outdoor trick-or-treating for children

March Farm Fall Festival

Bethlehem 37 mi $$

Pick-your-own apples and pumpkins with a 5-acre corn maze

Illustration of costumed children and a cat walking a leafy sidewalk past glowing jack-o'-lanterns and cozy houses at dusk (New London Halloween Town)

New London Halloween Town

New London 31 mi Free

Community Halloween celebration with trick-or-treating and costume contest.

Lenny Bruno Farms Fall Festival

Manorville 30 mi $

Over 8 acres of pumpkin fields and a corn maze.

Happy Hauntings Weekend

Bozrah 33 mi $$

Weekend of Halloween activities including trick-or-treating and contests.

Family-Friendly Fall Activities this weekend Oct 23–25

Sat24Oct Bats, Barnacles & Broomsticks Halloween PartyRiverhead

Sat24Oct Enchanted Forest Trail at Quogue Wildlife RefugeQuogue

Sat24Oct West Hartford Halloween StrollWest Hartford

Sat24Oct Día de Muertos Community CelebrationHartford

Sat24Oct Halloween at the FarmYaphank

Sun25Oct Spooktacular on the Green

Other Halloween categories in Guilford

Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights

GuilfordHalloween Food, Drink, and Parties9 parties & tastings

Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and black cats under a full moon at dusk

GuilfordHaunted Experiences13 haunted attractions

Illustration of a pumpkin character and a ghost performing on a lit stage with red curtains before a crowd at night

GuilfordHalloween Movies, Theater, and Entertainment3 shows & screenings

Illustration of a Halloween town at twilight with glowing houses, jack o lanterns, ghosts, and a witch flying past the moon

GuilfordUnique Halloween Events7 unique events

About Family-Friendly Fall Activities in Guilford

Guilford and surrounding towns offer Halloween activities for families. From pumpkin patches and festivals to creative workshops and themed runs, there are many ways to celebrate the season in areas like Middlefield, Milford, and even further afield in Methuen or New Haven.

Consider a free family fun day in New Haven, or a classic pumpkin festival at a local orchard, for different kinds of seasonal outings.

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Halloween Events Near Me

43 family-friendly fall activities in Guilford and nearby

Family-Friendly Fall Activities this weekend Oct 23–25

Other Halloween categories in Guilford

About Family-Friendly Fall Activities in Guilford

Find Family-Friendly Halloween Fun on Our Map!